The Tax Advantages of Real Estate Investing: Our Journey to Financial Freedom
- Jolie Keenan

- Dec 21, 2024
- 2 min read
Updated: Dec 21, 2024
DISCLAIMER: I am not a tax accountant, I am not a tax attorney, I am not a financial advisor. Please consult with your own legal professionals.

When we first considered real estate investing, one factor stood out above all others: the incredible tax benefits. Through our four-year journey in real estate investing, we've discovered just how powerful these advantages can be. I'd highly recommend reading "Tax Free Wealth" by Tom Wheelwright and "The Book on Tax Strategies for the Savvy Real Estate Investor" by Amanda Han and Matthew Macfarland to deepen your understanding of these concepts.
Why are real estate tax benefits so substantial? It's by design. The government incentivizes real estate investment because property investors provide essential housing and contribute to employment. Let me share the key tax strategies that have transformed our investment approach:
1. Business and Expense Deductions
Real estate investors can deduct a wide range of business-related expenses, including:
Property taxes
Insurance premiums
Mortgage interest
Educational courses and coaching
Legal and professional fees
2. Real Estate Professional Status
This powerful strategy works particularly well for couples where one partner can dedicate significant time to real estate activities. When one spouse qualifies as a real estate professional, they can use property losses to offset their partner's W-2 income. However, this status comes with specific requirements that must be carefully followed.
3. Short-Term Rental Strategy
For active short-term rental investors, there's a valuable opportunity to deduct up to 60% of the property's depreciation losses against W-2 income in the first year. This percentage decreases by 20% each subsequent year. Like other strategies, this requires meeting specific criteria and careful planning.
4. 1031 Exchange: The Key to Building Generational Wealth
Instead of paying capital gains tax when selling an underperforming property, investors can use a 1031 exchange to roll those gains into a similar property. This strategy allows you to defer taxes indefinitely, potentially passing the appreciated properties to your descendants. It's a powerful tool for building lasting wealth, though it requires careful adherence to specific rules.
5. Depreciation: The Power of Paper Losses
Even while your property appreciates in value, tax law allows you to claim depreciation over 27.5 years. For example, with a $300,000 property, you can claim approximately $10,909 in annual depreciation losses. These "paper losses" can offset your real estate income without affecting your actual cash flow.
Our Real Results
These strategies aren't just theoretical – we've implemented most of them with our real estate tax accountant's guidance. The results have been remarkable:
Tax-free cash flow from our rental properties
$37,000 tax refund in 2023
$21,000 tax refund in 2024
Reinvestment of tax refunds into additional properties
Beyond the tax benefits, we've gained:
Property appreciation
Mortgage paydown by tenants
Increased equity
Consistent cash flow
This combination of benefits makes real estate investing incredibly worthwhile for us, creating a powerful cycle of wealth building.
Ready to Start Your Real Estate Journey?
Take the first step by downloading my free Real Estate Investment Financial Planning Workbook. This resource will help you evaluate your current financial position and prepare for your first investment property.
To your wealth and success,
Jolie



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